Pyrimidine derivatives having a herbicidal action and an action regulating plant growth

ABSTRACT

N-Pyrimidin-4-yl-N&#39;-sulfonylureas of the formula I and the basic addition salts thereof have herbicidal properties and properties for regulating, especially inhibiting, plant growth: ##STR1## the symbols in this formula having the following meanings: Q is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, amino, lower alkyl or dialkylamino, lower alkoxycarbonyl, formyl, lower alkoxyalkyl, lower alkoxyalkoxy, lower alkylthio, lower alkylsulfinyl or alkylsulfonyl, C 1  -C 4  -alkenyl or C 1  -C 4  -alkynyl, 
     R 1  is hydrogen, halogen, nitro, a ketal radical, a carbonyl radical substituted by allyl, haloalkyl, alkoxy or cycloalkyl, or is an oxime radical, a lower alkoxy, lower alkylthio, lower alkyl, lower alkylsulfinyl or sulfonyl group, 
     R 2  and R 3  independently of one another are each hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower alkoxyalkyl, lower alkoxyalkoxy, amino, lower alkyl- or dialkylamino or cyclopropyl, and R 2  and Q together can also form a 2-4-membered carbon chain, which is optionally interrupted by an oxygen or sulfur atom or by the group --NR 5  --, 
     R 4  is hydrogen, halogen, lower alkyl, methoxy, nitro or trifluoromethyl, 
     R 5  is hydrogen, C 1  -C 4  -alkyl or C 3  -C 4  -alkenyl, 
     X is oxygen, sulfur, --NR 5  --, ##STR2##  --CH═CH-- or an annularly-linked phenyl ring, and Z is oxygen or sulfur.

This is a continuation of application Ser. No. 780,547 filed on Sept.26, 1985, abandoned, which is a continuation of application Ser. No.610,223, filed on May 14, 1984, abandoned.

The present invention relates to novel N-pyrimidin-4-yl-N'-sulfonylureashaving a herbicidal action and an action regulating plant growth, toprocesses for producing them, to compositions containing them as activeingredients, and to the use thereof for controlling weeds, particularlyin crops of useful plants, or for regulating and reducing plant growth.

The N-pyrimidin-4-yl-N'-sulfonylureas according to the inventioncorrespond to the formula I ##STR3## wherein Q is halogen, C₁ -C₄-alkyl, C₁ -C₄ -haloalkyl, C_(1-C) ₄ -alkoxy, C₁ -C₄ -haloalkoxy, nitro,amino, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, cyano, C₁ -C₄-alkoxycarbonyl, formyl, C₂ -C₄ -alkoxyalkyl, C₁ -C₄ -alkylthio, C.sub.-C₄ -alkylsulfinyl, C₁ -C₄ -alkylsulfonyl, C₁ -C₄ -alkenyl or C₁ -C₄-alkynyl,

R₁ is hydrogen, halogen, nitro or a radical ##STR4## --SO₂ NR₇ R₈,--COR₉ or --(Y)_(m) --R₁₀, R₂ and R₃ independently of one another areeach hydrogen, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₂ -C₄ -alkoxyalkyl,C₂ -C₄ -alkoxyalkoxy, amino, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino orcyclopropyl, and Q and R₂ together can also form a 2-4-membered carbonchain, which is optionally interrupted by an oxygen or sulfur atom or bythe group N--R₅,

R₄ is hydrogen, halogen, C₁ -C₄ -alkyl, methoxy, nitro ortrifluoromethyl,

R₅ is hydrogen, C₁ -C₄ -alkyl or C₃ -C₄ -alkenyl,

X is oxygen, sulfur, --NR₅ --, ##STR5## --CH═CH-- or an annularly-linkedphenyl ring, Z is oxygen or sulfur,

R₆ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₄-C₇ -cycloalkylalkyl or C₂ -C₄ -alkoxyalkyl,

R₇ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -cyanoalkyl, methoxy or ethoxy,

R₈ is the same as R₅, or

R₇ and R₈ together with the nitrogen atom linking them form a 5- or6-membered saturated heterocycle optionally containing an oxygen orsulfur atom as ring member,

R₉ is C₁ -C₄ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₂ -C₆-haloalkoxy, C₁ -C₄ -cyanoalkoxy, C₁ -C₄ -alkylthio, C₃ -C₄-alkenylthio, C₃ -C₄ -alkynylthio, C₅ -C₆ -cycloalkoxy, C₄ -C₇-cycloalkylalkoxy, --NR₇ R₈ or C₂ -C₆ -alkoxyalkoxy,

R₁₀ is C₁ -C₄ -alkyl, unsubstituted or mono- or polysubstituted byhalogen, cyano, methoxy, ethoxy, nitro, C₁ -C₂ -alkyl-S(O)_(n), C₁ -C₂-haloalkoxy, C₁ -C₂ -haloalkylthio, --COR₆, --COR₉ or --SO₂ NR₇ R₈, oris C₂ -C₄ -alkenyl, unsubstituted or mono- or polysubstituted byhalogen, nitro, cyano, methoxy, ethoxy or C₁ -C₂ -alkyl-(S)O_(n), or isC₂ -C₄ -alkynyl,

m is zero or 1,

n is zero, 1 or 2,

W is oxygen or the group ═N--O--R₅, and

Y is oxygen, sulfur, --SO-- or --SO₂ --,

with the proviso that in the radical R₁ in the group --(Y)_(m) --R₁₀,R₁₀ is only C₃ -C₄ -alkynyl when m is 1.

The invention embraces also the salts of these sulfonylureas.

N-Pyrimidin-4-yl-N'-sulfonylureas unsubstituted in the 5-position of thepyrimidine ring and having herbicidal activity are known, for examplefrom the European Offenlegungsschriften Nos. EP-A 1485, 13 480 and 44212.

N-Pyrimidin-2-yl-N'-sulfonylureas substituted in the 5-position andhaving a herbicidal action are known from the U.S. Pat. No. 4,342,587.

And N-pyrimidin-4-yl-N-alkylsulfonylureas substituted in the 5-positionand having herbicidal activity are moreover described in European PatentApplication No. EP-A No. 61 661.

The present N-pyrimidin-4-yl-sulfonylureas which are substituted in the5-position of the pyrimidine ring by a radical Q are novel. They aredistinguished by an excellent herbicidal, selective-herbicidal andplant-growth-regulating action, the desired effect being obtained withapplied amounts of less than 1 kg per hectare.

In the definitions of R₁ to R₁₁, an alkyl group is straight-chain orbranched-chain, for example: methyl, ethyl, n-propyl, i-propyl, the fourisomeric butyl groups, n-amyl, i-amyl, 2-amyl or 3-amyl; the alkyl groupis preferably however straight-chain.

By alkoxy in the definitions is meant: methoxy, ethoxy, n-propyloxy,i-propyloxy and the four isomeric butyloxy groups, especially howevermethoxy or ethoxy.

Examples of alkylthio are methylthio, ethylthio, n-propylthio,i-propylthio and n-butylthio, particularly methylthio and ethylthio.

Examples of alkenyl groups are: vinyl, allyl, isopropenyl, 1-propenyl,1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl, 2-isobutenyl, 1-pentenyl,2-pentenyl, 3-pentenyl and 4-pentenyl, in particular however vinyl,allyl and 4-pentenyl.

Alkynyl groups are for example: ethinyl, propargyl, 1-propynyl, thethree isomeric butynyl groups as well as 4-pentynyl, but preferably thepropargyl group.

By halogen is meant in the above definitions and also in haloalkyl:fluorine, chlorine, bromine and iodine, preferably however fluorine andin particular chlorine.

In the definitions, cycloalkyl is for example: cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, preferably cyclopropyl, cyclopentyl orcyclohexyl.

The invention embraces likewise the salts which the compounds of theformula I can form with amines, alkali metal bases and alkaline-earthmetal bases or quaternary ammonium bases.

Alkali metal hydroxides and alkaline-earth metal hydroxides to beemphasised as salt formers are hydroxides of lithium, sodium, potassium,magnesium or calcium, especially those of sodium and potassium.

Examples of amines suitable for salt formation are: primary, secondaryand tertiary aliphatic and aromatic amines, such as methylamine,ethylamine, propylamine, i-propylamine, the four isomeric butylamines,dimethylamine, diethylamine, diethanolamine, dipropylamine,diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine,trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine,quinoline, and i-quinoline, particularly ethyl-, propyl-, diethyl- ortriethylamine, especially isopropylamine and diethanolamine.

Examples of quaternary ammonium bases are in general the cations ofhaloammonium salts, for example: the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation, thetetraethylammonium cation or the trimethylethylammonium cation, and alsothe ammonium cation.

The best effects have been obtained with the compounds corresponding tothe following formula: ##STR6## wherein Q, R₁ and R₂ have the meaningsdefined in the foregoing, whilst R₃ is C₁ -C₂ -alkyl, C₁ -C₂ -haloalkyl,cyclopropyl, C₁ -C₃ -alkoxy, C₁ -C₂ -haloalkoxy, methylthio ordifluoromethylthio.

Compounds of the formula Ia which have proved to be particularlyeffective are those in which

Q is halogen, C₁ -C₄ -alkyl, nitro, amino, formyl, methylthio,methylsulfinyl or methylsulfonyl,

R₁ is halogen, nitro, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₃ -C₄ -alkenyloxy, C₂ -C₄ -haloalkenyloxy, C₁ -C₄-haloalkylthio, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl ordimethylsulfamoyl,

R₂ is halogen, C₁ -C₃ -alkyl, cyclopropyl, C₁ -C₃ -alkoxy, C₁ -C₂-haloalkoxy, amino, methylamino, dimethylamino or difluoromethylthio,and

R₃ is C₁ -C₂ -alkyl, C₁ -C₂ -haloalkyl, cyclopropyl, C₁ -C₃ -alkoxy, C₁-C₂ -haloalkoxy, methylthio or difluoromethoxy;

particularly however those compounds in which Q has the above meaning,and

R₁ is halogen, nitro, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₄-haloalkylthio, C₁ -C₄ -alkoxycarbonyl or dimethylsulfamoyl,

R₂ is halogen, C₁ -C₂ -alkyl, C₁ -C₂ -alkoxy, C₁ -C₂ -haloalkoxy,methylamino or dimethylamino, and

R₃ is C₁ -C₂ -alkoxy, trifluoroethoxy or difluoromethoxy.

The following individual compounds are distinguished by virtue of theirgood action:

N-(2-methoxycarbonylphenylsulfonyl)-N'-(2,6-dimethoxy-5-methylpyrimidin-4-yl)urea; and

N-(2-difluoromethoxyphenylsulfonyl)-N'-(2,6-dimethoxy-5-methylpyrimidin-4-yl)urea.

The compounds of the formula I are produced, in a manner known per se,in an inert organic solvent.

According to one process, the compounds of the formula I are produced byreacting a sulfonamide of the formula I are produced by reacting asulfonamide of the formula II ##STR7## wherein R₁, R₄ and X have thesame meanings defined in the foregoing, in the presence of a base, witha pyrimidin-4-yl-carbamate of the formula III ##STR8## wherein Q, R₂, R₃and R₅ have the meanings defined under the formula I; and optionallyconverting the product obtained into a salt.

According to a second process, compounds of the formula I are obtainedby reacting a phenylsulfonylisocyanate of the formula IV ##STR9##wherein R₁, R₄ and X have the meanings defined in the foregoing,optionally in the presence of a base, with an amine of the formula V##STR10## wherein Q, R₂, R₃ and R₅ have the meanings given above; andoptionally converting the product obtained into a salt.

According to a further process, the compounds of the formula I in whichR₅ is hydrogen are produced by reacting a sulfonamide of the above-givenformula II, optionally in the presence of a base, with an isocyanate ofthe formula VI ##STR11## wherein Q, R₂ and R₃ have the meanings definedin the foregoing; and optionally converting the product obtained into asalt.

Finally, the compounds of the formula I can be obtained also by reactingan N-phenylsulfonylcarbamate of the formula VII ##STR12## wherein R₁, R₄and X have the meanings defined in the foregoing, with an amine of theformula V given above; and optionally converting the product obtainedinto a salt.

The resulting ureas of the formula I can if required be converted, bymeans of amines, alkali metal hydroxides or alkaline-earth metalhydroxides or quaternary ammonium bases, into basic addition salts. Thisis effected for example by reaction with the equimolar amount of a base,and removal of the solvent by evaporation. Such reactions are known, andare described for example in the U.S. Pat. Nos. 2,384,757 and 3,410,887.

The starting materials of the formulae II to VII are in part known, andcan be produced by generally known methods.

Thus, the sulfonamides of the formula II can be obtained from thecorresponding amines by diazotisation and exchange of the diazo groupfor sulfur dioxide in the presence of a catalyst, such as copper(II)chloride, in acetic acid, in the process of which the sulfonyl chlorideis formed (cp. J. Org. Chem. 25, 1824 (1960)); and subsequent reactionof the formed sulfonyl chloride with an ammonium hydroxide solution.

The sulfonylisocyanates of the formula IV can be obtained by reaction ofthe sulfonamides of the formula II with phosgene in the presence ofbutylisocyanate, in a chlorinated hydrocarbon as solvent, at therefluxing temperature (cp. in this respect "Newer Methods of PreparativeOrganic Chemistry", Vol. VI, 223-241, Academic Press, New York andLondon).

Amines of the formula V are known and some are obtainable commercially,or they can be produced by known methods (cp. "The Chemistry ofHeterocyclic Compounds", Viol. XVI+Suppl. I, Interscience Publishers,New York and London).

The isocyanates of the formula VI can be produced by reaction of aminesof the formula V with phosgene or oxalyl chloride in a chlorinatedhydrocarbon as solvent.

The sulfonylcarbamates of the formula VII are obtained by reaction ofthe sulfonamide of the formula II with diphenylcarbamate in the presenceof a base (cp. Japanese Patent Specification No. 61 169).

The carbamates of the formula III are obtained from the amines of theformula V in an analogous manner.

These reactions are advantageously performed in aprotic, inert organicsolvents, such as methylene chloride, tetrahydrofuran, acetonitrile,dioxane or toluene.

The reaction temperatures are preferably between -20° and +120° C. Thereactions proceed in general slightly exothermically and can beperformed at room temperature. For the purpose of shortening thereaction time or of initiating the reaction, heat is advantageouslyapplied for a short time up to the boiling point of the reactionmixture. The reaction times can be if required shortened by the additionof a few drops of a base or isocyanate as a reaction catalyst.

The final products can be isolated by concentration by evaporationand/or by evaporating off the solvent, and purified by recrystallisationor trituration of the solid residue in solvents in which the products donot readily dissolve, such as ethers, aromatic hydrocarbons orchlorinated hydrocarbons.

The active substances of the formula I are stable compounds, and thehandling of them requires no special precautions.

The compounds of the formula I are distinguished by goodselective-herbicidal properties, which render them excellently suitablefor use in crops of cultivated plants, for example in crops of wheat,maize and soya-bean. It is possible to some cases also to destroy weedswhich could be dealt with hitherto only by the application of totalherbicides.

The mode of action of these herbicides is unusual: they are capable ofbeing translocated, that is to say, they are taken up by the plant andtransported to other locations, where they produce the desired effect.The unusual feature is not only that they take the path of the nutrientsthrough the vascular bundle in the xylem from the roots into the leaves,but also that they can be translocated through the sieve tubes in thebast part from the leaves back into the roots. It is thus possible forexample by surface treatment of perennial weeds to destroy them at theroots. The novel compounds of the formula I are effective in appliedamounts which are very small compared with the amounts required toobtain the same effect using other herbicides.

The compounds of the formula I also have excellent properties forregulating plant growth, the effects of which can mean an increase inthe yield of cultivated plants or of harvested crops. Many compounds ofthe formula I exhibit moreover an action reducing plant growth to anextent depending on the concentration used. Both monocotyledons anddicotyledons are impaired in their growth.

Thus, for example, the leguminosae frequently planted as cover crops inagriculture in tropical regions can be selectively inhibited in theirgrowth by the compounds of the formula I, the result being that soilerosion between the cultivated plants is prevented, without the covercrops being able to compete with the main cultivated crop.

A reduction of the vegetative growth enables in the case of manycultivated plants the crop density to be increased, so that higheryields for the same area of land can be achieved.

An additional factor contributing to the increase in yield with the useof growth inhibitors is that the formation of blossom and fruit benefitsto a greater extent from the nutritive substances, because thevegetative growth is restricted.

In the case of monocotyledonous plants, for example grasses, orcultivated plants such as cereals, a reduction of vegetative growth issometimes desirable and advantageous. A reduction of growth of this kindis of economic interest with regard to, amongst other things, grasses,for as a consequence it is possible to reduce the frequency of thecutting of grass in ornamental gardens, parks and sports grounds, oralong the verges of highways. Of importance also is the inhibition ofthe growth of herbaceous and ligneous plants at the edges of roads andin the vicinity of overhead transmission lines, or quite generally inareas where a strong growth is undesirable.

Also important is the application of growth regulators for reducing thegrowth in height of cereals, since a shortening of the stems lessens orcompletely removes the danger of the snapping off (flattening) of theplants before harvesting. Furthermore, growth regulators can result in astrengthening of the stems of cereal crops, a further factor acting toprevent bending of the stems of the plants.

The compounds of the formula I are likewise suitable for preventing thesprouting of stored potatoes. Shoots frequently form on potatoes beingstored during the winter, and these shoots cause shrinkage, loss inweight and rotting.

With larger applied amounts of active substance, all the tested plantsare impaired in their development to the extent that they wither.

The present invention relates also to herbicidal andplant-growth-regulating compositions containing a novel activeingredient of the formula I, and also to processes for the pre- andpost-emergence controlling of weeds, and for the reduction of growth ofmonocotyledonous and dicotyledonous plants, particularly that ofgrasses, tropical cover crops and side shoots of tobacco plants.

The compounds of the formula I are used either in an unmodified form orpreferably in compositions, together with auxiliaries customarilyemployed in formulation practice, and are thus processed, in a knownmanner, for example into the form of emulsion concentrates, directlysprayable or dilutable solutions, diluted emulsions, wettable powders,soluble powders, dusts or granulates, and also encapsulations in forexample polymeric substances. The application processes, such asspraying, atomising, dusting, scattering or pouring, and likewise thetype of compositions, are selected to suit the objects to be achievedand the given conditions.

The formulations, that is to say, the compositions or preparationscontaining the active ingredient of the formula I and optionally a solidor liquid additive, are produced in a known manner, for example by theintimate mixing and/or grinding of the active ingredients withextenders, such as with solvents, solid carriers and optionallysurface-active compounds (tensides).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionsC₈ to C₁₂, such as xylene mixtures or substituted naphthalenes, phthalicesters, such as dibutyl- or dioctylphthalate, aliphatic hydrocarbons,such as cyclohexane or paraffins, alcohols and glycols, as well asethers and esters thereof, such as ethanol, ethylene glycol, ethyleneglycol monomethyl or -ethyl ethers, ketones, such as cyclohexanone,strongly polar solvents, such as N-methyl-2-pyrrolidone,dimethylsulfoxide or dimethylformamide, as well as optionally epoxidisedvegetable oils, such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used, for example for dusts and dispersible powders,are as a rule natural mineral fillers, such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties, it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, ground brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. There can also be used a great number of pre-granulatedmaterials of inorganic or organic nature, such as in particular dolomiteor ground plant residues.

Suitable surface-active compounds are, depending on the nature of theactive substance of the formula I to be formulated, nonionic, cationicand/or anionic tensides having good emulsifying, dispersing and wettingproperties. By `tensides` are also meant mixtures of tensides.

Suitable anionic tensides are both so-called water-soluble soaps as wellas water-soluble, synthetic, surface-active compounds.

Soaps which are applicable are the alkali metal, alkaline-earth metal oroptionally substituted ammonium salts of higher fatty acids (C₁₀ -C₂₂),for example the Na or K salts of oleic or stearic acid, or of naturalfatty acid mixtures, which can be obtained for example from coconut oilor tallow oil. Also to be mentioned are the fatty acid-methyl-taurinesalts.

So-called synthetic tensides are however more frequently used,particularly fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates. The fatty sulfonates or sulfates areas a rule in the form of alkali metal, alkaline-earth metal oroptionally substituted ammonium salts, and contain an alkyl group having8 to 22 C atoms, `alkyl` including also the alkyl moiety of acyl groups,for example the Na or Ca salts of ligninsulfonic acid, ofdodecylsulfuric acid ester or of a fatty alcohol sulfate mixtureproduced from natural fatty acids. Included among these are also thesalts of sulfuric acid esters and sulfonic acids of fatty alcoholethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and a fatty acid group having8-22C atoms. Alkylarylsulfonates are for example the Na, Ca ortriethanolamine salts of dodecylbenzenesulfonic acid, ofdibutylnaphthalenesulfonic acid or of a naphthalenesulfonicacid-formaldehyde condenation product. Also suitable are correspondingphosphates, for example salts of the phosphoric ester of ap-nonylphenol-(4-14)-ethylene oxide adduct, and phospholipides.

Suitable nonionic tensides are in particular polyglycol etherderivatives of aliphatic or cycloaliphatic alcohols, saturated orunsaturated fatty acids and alkylphenols, which contain 3 to 30 glycolether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbonradical and 6 to 18 carbon atoms in the alkyl moiety of thealkylphenols.

Further suitable nonionic tensides are the water-soluble polyethyleneoxide adducts, which contain 20 to 250 ethylene glycol ether groups and10 to 100 propylene glycol ether groups, with polypropylene glycol,ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usuallycontain 1 to 5 ethylene glycol units per propylene glycol unit. Examplesof nonionic tensides which may be mentioned are:nonylphenolpolyethoxyethanol, castor oil polyglycol ethers,polypropylene/polyethyleneoxy adducts, tributylphenoxypolyethoxyethanol,polyethylene glycol and octylphenoxypolyethoxyethanol. Suitable also arefatty acid esters of polyoxyethylenesorbitan, such aspolyoxyethylenesorbitan-trioleate.

In the case of the cationic tensides, they are in particular quaternaryammonium salts which contain as N-substituents at least one alkyl grouphaving 8 to 22C atoms and, as further substituents, lower, optionallyhalogenated alkyl, benzyl or lower hydroxyalkyl groups. The salts arepreferably in the form of halides, methyl sulfates or ethyl sulfates,for example stearyltrimethylammonium chloride orbenzyldi(2-chloroethyl)ethylammonium bromide.

The tensides customarily used in formulation practice are described,inter alia, in the following publications:

"Mc Cutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp.,Ridgewood, N.J., 1979;

M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, ChemicalPublishing Co., Inc. New York 1980-1981;

H. Stache, "Tensid Taschenbuch", 2nd Edition, C. Hanser Verlag, Munichand Vienna, 1981.

The agrochemical preparations contain as a rule 0.1 to 95%, especially0.1 to 80%, of active ingredient of the formula I, 1 to 99.9% of a solidor liquid additive, and 0 to 25%, particularly 0.1 to 25% of a tenside.

Preferred formulations are made up in particular as follows (%=percentby weight):

Emulsifiable concentrates

active ingredient: 1 to 20%, preferably 5 to 10%

surface active agent: 5 to 30%, preferably 10 to 20%

liquid carrier: 50 to 94%, preferably 70 to 85%.

Dusts

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%.

Suspension concentrates

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 25%, preferably 90 to 30%

surface-active agent: 1 to 40%, preferably 2 to 30%.

Wettable powders

active ingredient: 0.5 to 90%, preferably 1 to 80%

surface-active agent: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 95%, preferably 15 to 90%.

Granulates

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%.

Whereas commercial products are preferably in the form of concentratedcompositions, the compositions employed by the end-user are as a rulediluted. The preparations can for application be diluted down to 0.001%of active ingredient. The applied amounts are usually 0.001 to 10 kg,preferably 0.025 to 5 kg, of active substance per hectare.

The compositions can also contain additives such as stabilisers,antifoaming agents, viscosity regulators, binders and adhesives, as wellas fertilisers or other active substances for obtaining special effects.

In the following Examples, parts and percentages relate to weight, andpressure values are given in millibars (mb) (1 mb=100 Pascal).

EXAMPLE 1 Production ofN-(2-methoxycarbonylphenylsulfonyl)-N'-(2,6-dimethoxy-5-methyl-pyrimidin-4-yl)-urea##STR13##

2.41 g of 2-methoxycarbonylphenylsulfonylisocyanate and 1.7 g of4-amino-2,6-dimethoxy-5-methyl-pyrimidine are stirred up with 40 ml ofabsolute dioxane at 80°-85° C. for 2 hours; and the formed suspension issubsequently fully concentrated by evaporation. From the residue arethen obtained, by recrystallisation from a mixture of acetone and ether,3.4 g ofN-(2-carboxymethylphenylsulfonyl)-N'-(2,6-dimethoxy-5-methyl-pyrimidin-4-yl)-urea,m.p. 195°-196° C.

The 4-amino-2,6-dimethoxy-5-methylpyrimidine required as intermediate isobtained as follows.

(a) Production of 5-methylbarbituric acid

46 g (2 mols) of sodium are dissolved in 1 liter of absolute ethanol ina 5-liter flask. To this solution are firstly added 348 g (2 mols) ofmethyl malonic acid methyl ester; and there is then added dropwise at70° C. with stirring, within about 5 minutes, a solution of 120 g (2mols) of urea in 1 liter of absolute ethanol. There is formed a thinsuspension, which is diluted with 3.5 liters of ethanol, refluxed for 16hours and afterwards cooled. There are subsequently added 2 liters ofwater and, for clearing, a filtering auxiliary (HiFlo) is introduced,and the suspension is filtered. Concentrated hydrochloric acid is thenadded until a Congo blue colour is indicated, and the mixture is left tostand for several hours in a cool place. A fine white crystallineprecipitate is formed, which is filtered and dried. The mother liquor isconcentrated by evaporation, diluted with water, and the precipitate islikewise filtered and dried. The crude yield is 263 g of material, whichmelts at 200°-215° C. After recrystallisation from water, there remain144 g of white crystals (58% of theory), which melt at 203°-204° C.

(b) Production of 5-methyl-2,4,6-trichloropyrimidine

450 ml (2.94 mols) of phosphorus oxychloride are placed into a 2-literflask, and 49.3 ml (0.39 mol) of commercial N,N-dimethylaniline areslowly added with cooling and stirring. There are then addedportionwise, within 20 minutes, 142 g (1 mol) of methylbarbituric acid,which produces an exothermic reaction. The reaction mixture is allowedto heat up, and is finally refluxed for 5 hours until the evolution ofgas has ceased. The suspension is subsequently slowly poured into water,care being taken that the temperature remains at 25°-30° C. The aqueoussuspension is filtered with suction, and the filter residue is dissolvedin 250 ml of dichloromethane; the solution is filtered until clear, andextracted twice with 250 ml of ice-water each time. The organic phase isthen dried, concentrated by evaporation, and the residue occurring incrystalline form is dried in vacuo. The yield is 126.7 g of crystalline5-methyl-2,4,6-trichloropyrimidine, which melts at 67°-68° C.(yield=64.2% of theory).

(c) Production of 4-amino-2,6-dichloro-5-methylpyrimidine

39.5 g (0.2 mol) of 5-methyl-2,4,6-trichloropyrimidine are dissolved in250 ml of dimethoxyethane, and ammonia gas is then introduced at roomtemperature until the solution is saturated. A white suspension isformed, which is stirred for 12 hours at room temperature; it issubsequently concentrated in a rotary evaporator, and 200 ml of waterare added to the residue. The formed suspension is filtered and theprecipitate is dried. The mother liquor is concentrated to half thevolume, filtered, and the precipitate is dried. There are thus obtained26.4 g of crude product, which is recrystallised from acetonitrile/water(5:1); m.p. 193°-194° C. (yield=75% of theory).

Analysis: calculated: C 33.74%, H 2.83%, N 23.61%, Cl 39.83%, found: C33.80%, H 2.87%, N 23.44%, Cl 39.51%.

(d) Production of 4-amino-2,6-dimethoxy-5-methylpyrimidine

A mixture of 10.7 g (0.06 mol) of5-methyl-4-amino-2,6-dichloropyrimidine, 100 ml of methanol and 22 g of30% sodium methylate (0.122 mol) is allowed to react at 120° C. for 20hours in an autoclave. After cooling, the grey reaction mixture isconcentrated in vacuo; the residue is taken up in 70 ml of water,stirred and then filtered. The residue is washed with water, dried andrecrystallised from carbon tetrachloride. There remain after drying 6.1g of 4-amino-5-methyl-2,6-dimethoxypyrimidine as white crystals, whichmelt at 60° C. (yield=60% of theory).

Analysis: calculated: C 49.70%, H 6.55%, N 24.84%, O 18.91%, found: C49.45%, H 6.42%, N 24.59%, O 19.84%.

The following compounds are produced in a manner analogous to thisExample: ##STR14##

                                      TABLE 1                                     __________________________________________________________________________                                               Phys. data                         No.                                                                              Q      R.sub.1   R.sub.2                                                                              R.sub.3                                                                             R.sub.4                                                                            R.sub.5                                                                          Z m.p. °C.                    __________________________________________________________________________    1.1                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.2                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 195-196°                    1.3                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.4                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.5                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.2 F                                                                           OCH.sub.3                                                                           H    H  O                                    1.6                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             cyclopropyl                                                                          OCH.sub.3                                                                           H    H  O                                    1.7                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             SCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.8                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.9                                                                              CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                                                            OCH.sub.3                                                                           H    H  O                                    1.10                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             NHCH.sub.3                                                                           OCH.sub.3                                                                           H    H  O                                    1.11                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             NH.sub.2                                                                             OCH.sub.3                                                                           H    H  O                                    1.12                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub. 2 CF.sub.3                                                                  OCH.sub.3                                                                           H    H  O 158-159°                    1.13                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             OCHF.sub.2                                                                           OCH.sub.3                                                                           H    H  O                                    1.14                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                           OCH.sub.3                                                                           H    H  O                                    1.15                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             Cl     OCH.sub.3                                                                           H    H  O                                    1.16                                                                             CH.sub.3                                                                             COOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                           H    H  O                                    1.17                                                                             Cl     COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.18                                                                             Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 188-189°                    1.19                                                                             Cl     COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.20                                                                             Cl     COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O 192-194°                    1.21                                                                             Cl     COOCH.sub.3                                                                             CH.sub.2 F                                                                           OCH.sub.3                                                                           H    H  O                                    1.22                                                                             Cl     COOCH.sub.3                                                                             cyclopropyl                                                                          OCH.sub.3                                                                           H    H  O                                    1.23                                                                             Cl     COOCH.sub.3                                                                             SCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.24                                                                             Cl     COOCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.25                                                                             Cl     COOCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                                                            OCH.sub.3                                                                           H    H  O                                    1.26                                                                             Cl     COOCH.sub.3                                                                             NHCH.sub.3                                                                           OCH.sub.3                                                                           H    H  O                                    1.27                                                                             Cl     COOCH.sub.3                                                                             NH.sub.2                                                                             OCH.sub.3                                                                           H    H  O                                    1.28                                                                             Cl     COOCH.sub.3                                                                             OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.29                                                                             Cl     COOCH.sub.3                                                                             OCHF.sub.2                                                                           OCH.sub.3                                                                           H    H  O                                    1.30                                                                             Cl     COOCH.sub.3                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                           OCH.sub.3                                                                           H    H  O                                    1.31                                                                             Cl     COOCH.sub.3                                                                             Cl     OCH.sub.3                                                                           H    H  O 198-200°                    1.32                                                                             Cl     COOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                           H    H  O                                    1.33                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.34                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 184-185°                    1.35                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.36                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.37                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              CH.sub.2 F                                                                           OCH.sub.3                                                                           H    H  O                                    1.38                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              cyclopropyl                                                                          OCH.sub.3                                                                           H    H  O                                    1.39                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              SCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.40                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.41                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              CH.sub.2 OC.sub.2 H.sub.5                                                            OCH.sub.3                                                                           H    H  O                                    1.42                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              NHCH.sub.3                                                                           OCH.sub.3                                                                           H    H  O                                    1.43                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              NH.sub.2                                                                             OCH.sub.3                                                                           H    H  O                                    1.44                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.45                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              OCHF.sub.2                                                                           OCH.sub.3                                                                           H    H  O                                    1.46                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              OC.sub.2 H.sub.4 OCH.sub.3                                                           OCH.sub.3                                                                           H    H  O                                    1.47                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              Cl     OCH.sub.3                                                                           H    H  O                                    1.48                                                                             CH.sub.3                                                                             OCHF.sub.2                                                                              OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                           H    H  O                                    1.49                                                                             Cl     OCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O 177-178°                    1.50                                                                             Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 190-191°                    1.51                                                                             Cl     OCHF.sub.2                                                                              C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.52                                                                             Cl     OCHF.sub.2                                                                              N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O 169-170°                    1.53                                                                             Cl     OCHF.sub.2                                                                              CH.sub.2 F                                                                           OCH.sub.3                                                                           H    H  O                                    1.54                                                                             Cl     OCHF.sub.2                                                                              cyclopropyl                                                                          OCH.sub.3                                                                           H    H  O                                    1.55                                                                             Cl     OCHF.sub.2                                                                              SCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.56                                                                             Cl     OCHF.sub.2                                                                              CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.57                                                                             Cl     OCHF.sub.2                                                                              CH.sub.2 OC.sub.2 H.sub.5                                                            OCH.sub.3                                                                           H    H  O                                    1.58                                                                             Cl     OCHF.sub.2                                                                              NHCH.sub.3                                                                           OCH.sub.3                                                                           H    H  O                                    1.59                                                                             Cl     OCHF.sub.2                                                                              NH.sub.2                                                                             OCH.sub.3                                                                           H    H  O                                    1.60                                                                             Cl     OCHF.sub.2                                                                              OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                           H    H  O                                    1.61                                                                             Cl     OCHF.sub.2                                                                              OCHF.sub.2                                                                           OCH.sub.3                                                                           H    H  O                                    1.62                                                                             Cl     OCHF.sub.2                                                                              OC.sub.2 H.sub.4 OCH.sub.3                                                           OCH.sub.3                                                                           H    H  O                                    1.63                                                                             Cl     OCHF.sub.2                                                                              Cl     OCH.sub.3                                                                           H    H  O                                    1.64                                                                             Cl     OCHF.sub.2                                                                              OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                           H    H  O                                    1.65                                                                             CH.sub.3                                                                             CF.sub.3  OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.66                                                                             CH.sub.3                                                                             CF.sub.3  OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.67                                                                             CH.sub.3                                                                             CF.sub.3  OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.68                                                                             CH.sub.3                                                                             CF.sub.3  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.69                                                                             CH.sub.3                                                                             CF.sub.3  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.70                                                                             CH.sub.3                                                                             CF.sub.3  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.71                                                                             CH.sub.3                                                                             CF.sub.3  OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.72                                                                             CH.sub.3                                                                             CF.sub.3  CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.73                                                                             Cl     CF.sub.3  OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.74                                                                             Cl     CF.sub.3  OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.75                                                                             Cl     CF.sub.3  OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.76                                                                             Cl     CF.sub.3  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.77                                                                             Cl     CF.sub.3  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.78                                                                             Cl     CF.sub.3  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.79                                                                             Cl     CF.sub.3  OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.80                                                                             Cl     CF.sub.3  OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                  H    H  O                                    1.81                                                                             Cl     CF.sub.3  CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.82                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.83                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.84                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.85                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.86                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.87                                                                             CH.sub.3                                                                             NO.sub.2  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.88                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.89                                                                             CH.sub.3                                                                             NO.sub.2  CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.90                                                                             CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                  H    H  O                                    1.91                                                                             Cl     NO.sub.2  OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.92                                                                             Cl     NO.sub.2  OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.93                                                                             Cl     NO.sub.2  OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.94                                                                             Cl     NO.sub.2  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.95                                                                             Cl     NO.sub.2  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.96                                                                             Cl     NO.sub.2  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.97                                                                             Cl     NO.sub.2  OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.98                                                                             Cl     NO.sub.2  OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                  H    H  O                                    1.99                                                                             Cl     NO.sub.2  CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.100                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.101                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.102                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.103                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.104                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.105                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.106                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.107                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.108                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                  H    H  O                                    1.109                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.110                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O 182-183°                    1.111                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.112                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.113                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.114                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.115                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                  H    H  O                                    1.116                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.117                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             Cl     C.sub.2 H.sub.5                                                                     H    H  O 199-200°                    1.118                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O 212-213°                    1.119                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.120                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.121                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.122                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O 218-219°                    1.123                                                                            Cl     OCHF.sub.2                                                                              CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.124                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.125                                                                            Cl     OCHF.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            H    H  O                                    1.126                                                                            Cl     OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                                                                  H    H  O                                    1.127                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O                                    1.128                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                     H    H  O                                    1.129                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            SCH.sub.3                                                                           H    H  O                                    1.130                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                   H    H  O                                    1.131                                                                            Cl     COOCH.sub.3                                                                             CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    H    H  O                                    1.132                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.2 CH.sub.3                                                                   OC.sub.2 H.sub.5                                                                    H    H  O                                    1.133                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                    H    H  O                                    1.134                                                                            Cl     COOCH.sub.3                                                                             CH.sub. 3                                                                            CH.sub.3                                                                            H    H  O 174-175°                    1.135                                                                            Cl     COOCH.sub.3                                                                             OCH.sub.3                                                                            Cl    H    H  O 215-218°                    1.136                                                                            F      COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.137                                                                            F      COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 181-182°                    1.138                                                                            F      COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.139                                                                            F      COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.140                                                                            NO.sub.2                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.141                                                                            NO.sub.2                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.142                                                                            NO.sub.2                                                                             COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.143                                                                            NO.sub.2                                                                             COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.144                                                                            NH.sub.2                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.145                                                                            NH.sub.2                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.146                                                                            NH.sub.2                                                                             COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.147                                                                            NH.sub.2                                                                             COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.148                                                                            CF.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.149                                                                            CF.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.150                                                                            CF.sub.3                                                                             COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.151                                                                            CF.sub.3                                                                             COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.152                                                                            CF.sub.3                                                                             COOCH.sub.3                                                                             F      N(CH.sub.3).sub.2                                                                   H    H  O 157-158°                    1.153                                                                            CF.sub.3                                                                             COOCH.sub.3                                                                             F      NHCH.sub.3                                                                          H    H  O 135-137°                    1.154                                                                            C.sub.2 H.sub.5                                                                      COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.155                                                                            C.sub.2 H.sub.5                                                                      COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.156                                                                            C.sub.2 H.sub.5                                                                      COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.157                                                                            C.sub.2 H.sub.5                                                                      COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.158                                                                            OCH.sub.3                                                                            COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.159                                                                            OCH.sub.3                                                                            COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.160                                                                            OCH.sub.3                                                                            COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.161                                                                            OCH.sub.3                                                                            COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.162                                                                            CHO    COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.163                                                                            CHO    COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 184-185°                    1.164                                                                            CHO    COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.165                                                                            CHO    COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.166                                                                            COOCH.sub.3                                                                          COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.167                                                                            COOCH.sub.3                                                                          COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.168                                                                            COOCH.sub.3                                                                          COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.169                                                                            COOCH.sub.3                                                                          COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.170                                                                            CH.sub.3                                                                             NO.sub.2  CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.171                                                                            CH.sub.3                                                                             NO.sub.2  OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 202-203°                    1.172                                                                            CH.sub.3                                                                             NO.sub.2  N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.173                                                                            CH.sub.3                                                                             NO.sub.2  C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.174                                                                            Cl     NO.sub.2  CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.175                                                                            Cl     NO.sub.2  OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.176                                                                            Cl     NO.sub.2  N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O 185-186°                    1.177                                                                            Cl     NO.sub.2  C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.178                                                                            CH.sub.3                                                                             CF.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.179                                                                            CH.sub.3                                                                             CF.sub.3  OCH.sub.3                                                                            OCH.sub. 3                                                                          H    H  O                                    1.180                                                                            CH.sub.3                                                                             CF.sub.3  N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.181                                                                            CH.sub.3                                                                             CF.sub.3  C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.182                                                                            Cl     CF.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.183                                                                            Cl     CF.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.184                                                                            Cl     CF.sub.2  N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.185                                                                            CL     CF.sub.3  C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.186                                                                            SCH.sub.3                                                                            COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.187                                                                            SCH.sub.3                                                                            COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.188                                                                            SCH.sub.3                                                                            COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.189                                                                            SCH.sub.3                                                                            COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.190                                                                            SOCH.sub.3                                                                           COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.191                                                                            SOCH.sub.3                                                                           COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.192                                                                            SOCH.sub.3                                                                           COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.193                                                                            SOCH.sub.3                                                                           COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.194                                                                            SO.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.195                                                                            SO.sub. 2 CH.sub.3                                                                   COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.196                                                                            SO.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.197                                                                            SO.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.198                                                                            CN     COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.199                                                                            CN     COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.200                                                                            CN     COOCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O                                    1.201                                                                            CN     COOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           H    H  O                                    1.202                                                                            CH.sub.3                                                                             COSCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.203                                                                            CH.sub.3                                                                             CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.204                                                                            CH.sub.3                                                                             CH.sub.2 SCH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.205                                                                            CH.sub.3                                                                             CH.sub.2 SOCH.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.206                                                                            CH.sub.3                                                                             CH.sub.2 SO.sub.2 CH.sub.3                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.207                                                                            CH.sub.3                                                                             C.sub.2 H.sub.4 OCH.sub.3                                                               OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.208                                                                            CH.sub.3                                                                             SCH.sub.2 CH═CH.sub.2                                                               OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.209                                                                            CH.sub.3                                                                             OCH.sub.2 CCl═CH.sub. 2                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.210                                                                            CH.sub.3                                                                             CH═CHCN                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.211                                                                            CH.sub.3                                                                             C.sub.3 H.sub.6 OCH.sub.3                                                               OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.212                                                                            CH.sub.3                                                                             CH.sub.2 COCH.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.213                                                                            CH.sub.3                                                                             OCH.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.214                                                                            CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 216-217°                    1.215                                                                            CH.sub.3                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.216                                                                            CH.sub.3                                                                             OCH.sub.2 CH═CH.sub.2                                                               OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.217                                                                            CH.sub.3                                                                             OCH.sub.2 CH.tbd.CH                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.218                                                                            CH.sub.3                                                                             OCF.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 189-190°                    1.219                                                                            CH.sub.3                                                                             OCF.sub.2 CHF.sub.2                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.220                                                                            CH.sub.3                                                                             OCF.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.221                                                                            CH.sub.3                                                                             OCH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 214-215°                    1.222                                                                            CH.sub.3                                                                             OCHCl═CHCl                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 222-223°                    1.223                                                                            CH.sub.3                                                                             CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.224                                                                            CH.sub.3                                                                             C.sub.2 H.sub.5                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.225                                                                            CH.sub.3                                                                             nC.sub.3 H.sub.7                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.226                                                                            CH.sub.3                                                                             SCF.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.227                                                                            CH.sub.3                                                                             CH.sub.2 Cl                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.228                                                                            CH.sub.3                                                                             C.sub.2 H.sub.4 CF.sub.3                                                                OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.229                                                                            CH.sub.3                                                                             Br        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.230                                                                            CH.sub.3                                                                             F         OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.231                                                                            CH.sub.3                                                                             SCH.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.232                                                                            CH.sub.3                                                                             SOCH.sub.3                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.233                                                                            CH.sub.3                                                                             SO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.234                                                                            CH.sub.3                                                                             SO.sub.2 C.sub.3 H.sub.7 n                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.235                                                                            CH.sub.3                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.236                                                                            CH.sub.3                                                                             CHO       OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.237                                                                            CH.sub.3                                                                             COCH.sub.3                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.238                                                                            CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.239                                                                            CH.sub.3                                                                             COOCH.sub.2 CH═CH.sub.2                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.240                                                                            CH.sub.3                                                                             OSO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.241                                                                            CH.sub.3                                                                             OSO.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.242                                                                            CH.sub.3                                                                             COCF.sub.3                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.243                                                                            CH.sub.3                                                                             CH═CH.sub.2                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.244                                                                            CH.sub.3                                                                             CH═CHCH.sub.3                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.245                                                                            CH.sub.3                                                                             CH═CCl.sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.246                                                                            CH.sub.3                                                                             CH═CHCF.sub.3                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.247                                                                            CH.sub.3                                                                             CH.sub.2 CN                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.248                                                                            CH.sub.3                                                                             CON(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.249                                                                            Cl     OCH.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           5-OCH.sub.3                                                                        H  O 201-203°                    1.250                                                                            SOCH.sub.3                                                                           Cl        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 161-165°                    1.251                                                                            NO.sub.2                                                                             Cl        Cl     C.sub.2 H.sub.5                                                                     H    H  O 119°                        1.252                                                                            CN     Cl        CH.sub.3                                                                             H     H    H  O 159- 161°                   1.253                                                                            CN     Cl        CH.sub.3                                                                             Cl    H    H  O 143-144°                    1.254                                                                            NO.sub.2                                                                             Cl        CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O 154-155°                    1.255                                                                            NO.sub.2                                                                             Cl        Cl     SCH.sub.3                                                                           H    H  O 75-80°                      1.256                                                                            NO.sub.2                                                                             Cl        NH.sub.2                                                                             SCH.sub.3                                                                           H    H  O 218-220°                    1.257                                                                            NO.sub.2                                                                             Cl        Cl     CH.sub.3                                                                            H    H  O 121-124°                    1.258                                                                            NO.sub.2                                                                             Cl        OCH.sub.3                                                                            CH.sub.3                                                                            H    H  O 190-192°                    1.259                                                                            Cl     SCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 184-185°                    1.260                                                                            F      OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 156-157°                    1.261                                                                            F      Cl        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 216-217°                    1.262                                                                            Br     COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O 177-178°                    1.263                                                                            NH.sub.2                                                                             Cl        CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O 175-178°                                                               decomp.                            1.264                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    CH.sub.3                                                                         O                                    1.265                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  S                                    1.266                                                                            CH.sub.3                                                                             Cl        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  S                                    1.267                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  S                                    1.268                                                                            CH.sub.3                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    CH.sub.3                                                                         O                                    1.269                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    CH.sub.3                                                                         O                                    1.270                                                                            Cl     OC.sub.2 H.sub.2 OCH.sub.3                                                              N(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           H    H  O 165-166°                    1.271                                                                            NO.sub.2                                                                             OCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O 145-146°                    1.272                                                                            CH.sub.3                                                                             Cl        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 221-222°                    1.273                                                                            F      COOCH.sub.3                                                                             H      OCH.sub.3                                                                           H    H  O 196-197°                    1.274                                                                            Cl     COOCH.sub.3                                                                             H      OCH.sub.3                                                                           H    H  O 190-192°                    1.275                                                                            CH.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             OCHF.sub.2                                                                           C.sub.3 H.sub.7 (n)                                                                 H    H  O 170-171°                    1.276                                                                            SO.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             OCH.sub.3                                                                            NHC.sub.3 H.sub.7 (i)                                                               H    H  O 231-233°                    1.277                                                                            SO.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             NHC.sub.3 H.sub.7 (i)                                                                OCH.sub.3                                                                           H    H  O 181-183°                    1.278                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                                                                  H    H  O 170-171°                    1.279                                                                            C.sub.3 H.sub.7 (i)                                                                  COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 170-171°                    1.280                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             Cl     CH.sub.2 OCH.sub.3                                                                  H    H  O 193-194°                    1.281                                                                            CH.sub.3                                                                             COOCH.sub.3                                                                             OCH.sub.2 CH.sub.3                                                                   CH.sub.2 OCH.sub.3                                                                  H    H  O 163-164°                    1.282                                                                            SCH.sub.3                                                                            COOCH.sub.3                                                                             OCH.sub.3                                                                            C.sub.3 H.sub.7 (i)                                                                 H    H  O 146-147°                    1.283                                                                            SOCH.sub.3                                                                           COOCH.sub.3                                                                             OCH.sub.3                                                                            C.sub.3 H.sub.7 (i)                                                                 H    H  O 167-168°                    1.284                                                                            SO.sub.2 CH.sub.3                                                                    COOCH.sub.3                                                                             OCH.sub.3                                                                            C.sub.3 H.sub.7 (i)                                                                 H    H  O 152-153°                    1.285                                                                            J      COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 175-176°                    1.286                                                                            --CH═CH.sub.2                                                                    COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 144-145°                    1.287                                                                            --C.tbd.CH                                                                           COOCH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O 146-149°                                                               decomp.                            1.288                                                                            Cl     OCH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.289                                                                            Cl     OC.sub.2 H.sub.2 OCH.sub.3                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.290                                                                            Cl     OCH.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.291                                                                            Cl     OCH.sub.2 CH.sub.3                                                                      OCH.sub. 3                                                                           OCH.sub.3                                                                           H    H  O                                    1.292                                                                            Cl     OCCl═CHCl                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.293                                                                            Cl     SCH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.294                                                                            Cl     OCF.sub.2 CHF.sub.2                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.295                                                                            Cl     OCF.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.296                                                                            Cl     Cl        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.297                                                                            Cl     F         OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.298                                                                            Cl     CH═CH--CF.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.299                                                                            Cl     SO.sub.2 N(CH.sub.3).sub.2                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.300                                                                            Cl     CON(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.301                                                                            F      OCH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.302                                                                            F      OC.sub.2 H.sub.4 OCH.sub.3                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.303                                                                            F      OCH.sub.3 OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.304                                                                            F      OCH.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.305                                                                            F      OCCl═CHCl                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.306                                                                            F      NO.sub.2  OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.307                                                                            F      OCH.sub.2 --CH═CH.sub. 2                                                            OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.308                                                                            Cl     OCH.sub.2 --CH═CH.sub.2                                                             OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.309                                                                            Cl     OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.310                                                                            Cl     OCH.sub.2 CH.sub.2 Cl                                                                   CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.311                                                                            Cl     OC.sub.2 H.sub.4 OCH.sub.3                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.312                                                                            Cl     OCH.sub.3 CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.313                                                                            Cl     OCH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.314                                                                            Cl     OCCl═CHCl                                                                           CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.315                                                                            Cl     OCH.sub.2 --CH═CH.sub.2                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.316                                                                            Cl     Cl        CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.317                                                                            Cl     F         CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.318                                                                            Cl     SCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.319                                                                            NO.sub.2                                                                             F         CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.320                                                                            NO.sub.2                                                                             SCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.321                                                                            NO.sub.2                                                                             OCH.sub.2 OCH.sub.2 Cl                                                                  CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.322                                                                            NO.sub.2                                                                             OCCl═CHCl                                                                           CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.323                                                                            NO.sub.2                                                                             OC.sub. 2 H.sub.4 OCH.sub.3                                                             CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.324                                                                            NO.sub.2                                                                             OCH.sub.2 CH═CH.sub.2                                                               CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.325                                                                            NO.sub.2                                                                             Cl        OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.326                                                                            NO.sub.2                                                                             F         OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.327                                                                            NO.sub.2                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.328                                                                            NO.sub.2                                                                             SCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.329                                                                            NO.sub.2                                                                             OCH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.330                                                                            NO.sub.2                                                                             OCCl═CHCl                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.331                                                                            NO.sub.2                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.332                                                                            NO.sub.2                                                                             OCH.sub.2 CH═CH.sub.2                                                               OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.333                                                                            NH.sub.2                                                                             OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.334                                                                            NH.sub.2                                                                             OCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.335                                                                            SOCH.sub.3                                                                           NO.sub.2  OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.336                                                                            SOCH.sub.3                                                                           NO.sub.2  CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    1.337                                                                            SOCH.sub.3                                                                           OCHF.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                           H    H  O                                    1.338                                                                            SOCH.sub.3                                                                           OCHF.sub.2                                                                              CH.sub.3                                                                             OCH.sub.3                                                                           H    H  O                                    __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                         ##STR15##                                                                    No.  R.sub.1     QR.sub.2    R.sub.3                                                                             R.sub.4                                                                             R.sub.5                                                                           Z                                ______________________________________                                        2.1  COOCH.sub.3 C.sub.3 H.sub.6                                                                           OCH.sub.3                                                                           H     H   O                                2.2  COOCH.sub.3 C.sub.4 H.sub.8                                                                           OCH.sub.3                                                                           H     H   O                                2.3  COOCH.sub.3 OC.sub.3 H.sub.6                                                                          OCH.sub.3                                                                           H     H   O                                2.4  COOCH.sub.2 C.sub.2 H.sub.4 O                                                                         OCH.sub.3                                                                           H     H   O                                ______________________________________                                    

                                      TABLE 3                                     __________________________________________________________________________     ##STR16##                                                                                                          Position                                                                      of the                                  No.                                                                              Q  R.sub.1    R.sub.2                                                                           R.sub.3                                                                           R.sub.4                                                                         R.sub.5                                                                         X      Z SO.sub.2 group                          __________________________________________________________________________    3.1                                                                              CH.sub.3                                                                         3-COOCH.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                         H H S      O 2                                       3.2                                                                              CH.sub.3                                                                         2-COOCH.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                         H H S      O 3                                       3.3                                                                              CH.sub.3                                                                         3-COOCH.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                         H H S      O 4                                       3.4                                                                              CH.sub.3                                                                         H          OCH.sub.3                                                                         OCH.sub.3                                                                         H H NH     O 2                                       3.5                                                                              CH.sub.3                                                                         H          OCH.sub.3                                                                         OCH.sub.3                                                                         H H NH     O 2                                       3.6                                                                              CH.sub.3                                                                         2-Cl       OCH.sub.3                                                                         OCH.sub.3                                                                         H H CHN    O 3                                       3.7                                                                              CH.sub.3                                                                         2-Cl       CH.sub.3                                                                          OCH.sub.3                                                                         H H CHN    O 3                                       3.8                                                                              CH.sub.3                                                                         3-COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                         H H CHN    O 2                                       3.9                                                                              CH.sub.3                                                                         2-COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                         H H CHN    O 3                                       3.10                                                                             CH.sub.3                                                                         3-COOCH.sub.3                                                                            CH.sub.3                                                                          OCH.sub.3                                                                         H H CHN    O 4                                       3.11                                                                             CH.sub.3                                                                         2-OCH.sub.2 CHCH.sub.2                                                                   CH.sub.2                                                                          OCH.sub.3                                                                         H H CHN    O 3                                       3.12                                                                             CH.sub.3                                                                         2-OCH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                         OCH.sub.3                                                                         H H CHN    O 3                                       3.13                                                                             CH.sub.3                                                                         2-OCH.sub.2 CH.sub.2 CH.sub.2                                                            CH.sub.3                                                                          OCH.sub.3                                                                         H H CHN    O 3                                       3.14                                                                             CH.sub.3                                                                         2-OCH.sub.3 CH.sub.2 CH.sub.3                                                            OCH.sub.3                                                                         OCH.sub.3                                                                         H H CHN    O 3                                       3.15                                                                             CH.sub.3                                                                         2-OCH.sub.3                                                                              CH.sub.3                                                                          OCh.sub.3                                                                         H H CHN    O 3                                       3.16                                                                             CH.sub.3                                                                         2-OCH.sub.3                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         H H CHN    O 3                                       3.17                                                                             CH.sub.3                                                                         2-OCH.sub.2 CHCHCH.sub.3                                                                 CH.sub.3                                                                          OCH.sub.3                                                                         H H CHN    O 3                                       3.18                                                                             CH.sub.3                                                                         2-OCH.sub.2 CHCHCH.sub.3                                                                 OCH.sub.3                                                                         OCH.sub.3                                                                         H H CHN    O 3                                       __________________________________________________________________________

                  TABLE 4                                                         ______________________________________                                         ##STR17##                                                                                                       Phys. data                                 No.  R.sub.1    R.sub.2    R.sub.3                                                                           R.sub.4                                                                           m.p. °C.                            ______________________________________                                        4.001                                                                              COOCH.sub.3                                                                              OCH.sub.3  H   H   179-180° decomp.                    4.002                                                                              COOCH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                       H   H   198-199°                            4.003                                                                              COOCH.sub.3                                                                              OCH.sub.2 CH.sub.3                                                                       H   H   178-180° decomp.                    4.004                                                                              COOCH.sub.3                                                                              N(CH.sub.3).sub.2                                                                        H   H                                              4.005                                                                              COOCH.sub.3                                                                              SCH.sub.3  H   H                                              4.006                                                                              COOCH.sub.3                                                                              Cl         H   H                                              4.007                                                                              COOCH.sub.3                                                                              CH.sub.3   H   H   177-178° decomp.                    4.008                                                                              NO.sub.2   OCH.sub.3  H   H                                              4.009                                                                              NO.sub.2   OCH.sub.2 CF.sub.3                                                                       H   H                                              4.010                                                                              NO.sub.2   Cl         H   H                                              4.011                                                                              NO.sub.2   OCH.sub.2 CH.sub.3                                                                       H   H                                              4.012                                                                              Cl         OCH.sub.3  H   H                                              4.013                                                                              Cl         OCH.sub.2 CF.sub.3                                                                       H   H                                              4.014                                                                              Cl         OCH.sub.2 CH.sub.3                                                                       H   H                                              4.015                                                                              Cl         Cl         H   H                                              4.016                                                                              OCHF.sub.2 OCH.sub.3  H   H                                              4.017                                                                              OCHF.sub.2 OCH.sub.2 CF.sub.3                                                                       H   H                                              4.018                                                                              OCHF.sub.2 OCH.sub.2 CH.sub.3                                                                       H   H                                              4.019                                                                              OCHF.sub.2 Cl         H   H                                              4.020                                                                              OCHF.sub.2 CH.sub.3   H   H                                              ______________________________________                                    

FORMULATION EXAMPLES EXAMPLE 2 Formulation Examples for activeingredients of the formula I (%=percent by weight)

    ______________________________________                                        (a) Wettable powder                                                                              (a)      (b)     (c)                                       ______________________________________                                        active ingredient  20%      60%       0.5%                                    sodium lignin sulfonate                                                                          5%       5%      5%                                        sodium lauryl sulfate                                                                            3%       --      --                                        sodium diisobutylnaphthalene                                                                     --       6%      6%                                        sulfonate                                                                     octylphenolpolyethylene glycol                                                                   --       2%      2%                                        ether (7-8 mols of ethylene oxide)                                            highly dispersed silicic acid                                                                    5%       27%     27%                                       kaolin             67%      --      --                                        sodium chloride    --       --       59.5%                                    ______________________________________                                    

The active ingredient is well mixed with the additives and ground in asuitable mill. There are obtained wettable powders which can be dilutedwith water to give suspensions of the concentration desired.

    ______________________________________                                        (b) Emulsion concentrate                                                                             (a)    (b)                                             ______________________________________                                        active ingredient      10%    1%                                              octylphenolpolyethylene glycol ether                                                                  3%    3%                                              (4-5 mols of ethylene oxide)                                                  calcium dodecyl benzene sulfonate                                                                     3%    3%                                              castor oil polyglycol ether                                                                           4%    4%                                              (36 mols of ethylene oxide)                                                   cyclohexanone          30%    10%                                             xylene mixture         50%    79%                                             ______________________________________                                    

Emulsions of the concentration desired can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dust           (a)     (b)                                                ______________________________________                                        active ingredient   0.1%    1%                                                talcum             99.9%   --                                                 kaolin             --      99%                                                ______________________________________                                    

Dusts ready for use are obtained by mixing the active-ingredient withthe carriers, and grinding the mixture in a suitable mill.

    ______________________________________                                        (d) Extruder granulate                                                                            (a)    (b)                                                ______________________________________                                        active ingredient   10%    1%                                                 sodium lignin sulfonate                                                                            2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed with the additives, and the mixture isthen ground and moistened with water. It is extruded and subsequentlydried in a stream of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        active ingredient    3%                                                       polyethylene glycol (MW 200)                                                                       3%                                                       kaolin               94%                                                      ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate                                                                          (a)      (b)                                            ______________________________________                                        active ingredient     40%      5%                                             ethylene glycol       10%      10%                                            nonylphenolpolyethylene glycol                                                                       6%      1%                                             ether (15 mols of ethylene oxide)                                             sodium lignin sulfonate                                                                             10%      5%                                             carboxymethylcellulose                                                                               1%      1%                                             37% aqueous formaldehyde solution                                                                     0.2%     0.2%                                         silicone oil in the form of a                                                                         0.8%     0.8%                                         75% aqueous emulsion                                                          water                 32%      77%                                            ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadditives. There is obtained a suspension concentrate from which can beproduced, by dilution with water, suspensions of the concentrationrequired.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        active ingredient      5%                                                     isopropylamine         1%                                                     octylphenolpolyethylene glycol ether                                                                 3%                                                     (78 mols of ethylene oxide)                                                   water                  91%                                                    ______________________________________                                    

EXAMPLE 3 Biological tests Verification of herbicidal action beforeemergence of the plants

Plastics pots are filled with expanded vermiculite (density: 0.135g/cm³, water-absorption capacity: 0.565 l/l). After saturation of thenon-adsorptive vermiculite with an aqueous active-ingredient emulsion indeionised water, which contains the active ingredient at a concentrationof 70.8 ppm, seeds of the following plants are sown on the surface:Nasturtium officinalis, Agrostis tenuis, Stellaria media and Digitariasanguinalis. The test vessels are subsequently kept in a climaticchamber at 20° C., with an illumination of about 20 k lux and a relativehumidity of 70%. During the germination phase of 4 to 5 days, the potsare covered over with light-permeable material in order to raise thelocal air humidity and watered with deionised water. After the 5th day,0.5% of a commercial liquid fertiliser (® Greenzit) is added to thewater. The test is evaluated 12 days after sowing, and the effect on thetest plants assessed according to the following scale of ratings:

1 plants have not germinated or are totally destroyed

2-3 very strong action

4-6 medium action

7-8 no action (as untreated control plants)

Pre-emergence action

Concentration of the active-ingredient emulsion: 70.8 ppm

    ______________________________________                                        Active   Test plant                                                           ingredient                                                                             Nasturtium                                                                              Stellaria Agrostis                                                                             Digitaria                                 No.      officinalis                                                                             media     tenuis sanguinalis                               ______________________________________                                        1.002    2         2         2      3                                         1.012    1         3         1      4                                         1.017    2         2         3      3                                         1.018    1         1         3      8                                         1.020    2         2         2      4                                         1.031    3         5         3      6                                         1.034    1         2         1      2                                         1.049    2         2         2      3                                         1.052    2         1         1      2                                         1.110    4         4         7      8                                         1.122    6         7         7      9                                         1.125    1         2         1      2                                         1.134    2         8         2      9                                         1.135    3         3         6      7                                         1.137    2         2         1      2                                         1.152    2         3         2      3                                         1.155    2         2         2      3                                         1.171    2         2         3      3                                         1.176    2         2         2      6                                         1.191    1         1         1      2                                         1.195    2         2         2      2                                         1.214    1         2         1      3                                         1.218    2         6         2      7                                         1.221    1         2         2      3                                         1.222    1         2         2      3                                         2.261    2         2         2      2                                         2.262    1         1         2      3                                         2.270    2         3         2      6                                         2.271    2         2         2      4                                         2.272    2         2         4      4                                         2.273    2         3         2      4                                         2.274    2         3         4      5                                         2.277    2         2         4      6                                         1.277    2         2         4      6                                         1.278    2         3         4      4                                         1.279    2         2         2      3                                         1.280    4         7         5      8                                         1.282    3         5         4      6                                         1.285    2         2         3      3                                         4.002    2         2         2      3                                         4.003    3         8         3      9                                         ______________________________________                                    

Verification of the herbicidal action before emergence of the plants

Plant seeds are sown in flower pots (12-15 cm in diameter) in agreenhouse. The surface of the soil is treated immediately afterwardswith an aqueous dispersion or solution of the active ingredients,obtained from a flowable or wettable powder. Various concentrationscorresponding to specific amounts of active ingredient per hectare areused. The pots are then kept in a greenhouse at a temperature of 22°-25°C. with 50-70% relative humidity. After 3 weeks, the tested compounds ofTables 1-4 exhibit a good action at concentrations of 0.03 to 1 kg perhectare.

Verification of the herbicidal action after emergence of the plants(contact action)

A considerable number of weeds and cultivated plants, bothmonocotyledonous and dicotyledonous, are sprayed after emergence, in the4- to 6-left stage, with an aqueous active-ingredient dispersion invarying dosages, and are then kept at 24° to 26° C. with 40-60% relativehumidity. The tested compounds of Tables 1-4 exhibit 15 days after thetreatment a good herbicidal action.

Verification of the reduction in growth of tropical leguminous covercrops

The test plants (Centrosema plumieri and Centrosema pubescens) arecultivated to the fully grown stage, and then cut back to a height of 60cm. After 7 days, the active ingredient is sprayed on in the form of anaqueous emulsion. The test plants are maintained at 70% relativehumidity and with 6000 lux of artificial light, 14 hours per day, attemperatures of 27° C. by day and 21° C. by night. The test results areassessed 4 weeks after application of the emulsion. The new growthoccurring compared with that on the control plants is estimated andweighed, and the phytotoxicity is evaluated. The plants treated with theactive ingredients from Tables 1-4 show in this test a clear reductionin new growth (less than 20% of the new growth occurring on untreatedcontrol plants), without the test plants having suffered damage.

Verification of reduction in growth of cereals

The cereal varieties Hordeum vulgare (spring barley) and Secale (springrye) are sown in plastics pots containing sterilised soil in agreenhouse, and watered as required. The young shoots are sprayed, about21 days after sowing, with the aqueous spray liquor of an activeingredient of the formula I. The amount applied is up to 100 g of activeingredient per hectare, and 21 days after application, the growth of thecereals is assessed. The treated plants show a reduction in the extentof new growth compared with that on the untreated control plants (60-90%of the new growth on the control plants), and also in part an increasedin the diameter of the stems of the plants.

Verification of reduction in growth of grasses

The grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylisglomerata and Cynodon dactylon are sown in a greenhouse, in plasticsdishes containing a soil/peat/sand mixture (6:3:1), and watered asrequired. The emerged grasses are cut back weekly to a height of 4 cm,and are sprayed, about 50 days after sowing and one day after the finalcutting, with the aqueous spray liquor of an active ingredient of theformula I. The amount of active ingredient corresponds, when converted,to up to 100 g per hectare. The growth of the grasses is assessed 21days after application.

The tested compounds of Tables 1-4 effect a reduction of new growthcompared with the new growth of the untreated control grasses.

What is claimed is:
 1. An N-pyrimidin-4-yl-N'-sulfonylurea of theformula Ia ##STR18## wherein Q is halogen, C₁ -C₄ -alkyl, nitro, amino,formyl, methylthio, methylsulfinyl or methylsulfonyl,R₁ is halogen,nitro, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₃ -C₄-alkenyloxy, C₂ -C₄ -haloalkenyloxy, C₁ -C₄ -haloalkylthio, C₁ -C₄-alkoxycarbonyl or C₁ -C₄ -alkylsulfonyl, R₂ is halogen, C₁ -C₃ -alkyl,cyclopropyl, C₁ -C₃ -alkoxy, C₁ -C₂ -haloalkoxy, amino, methylamino ordimethylamino, R₃ is C₁ -C₂ -alkyl, C₁ -C₂ -haloalkyl, cyclopropyl, C₁-C₂ -alkoxy, C₁ -C₂ -haloalkoxy or difluoromethoxy.
 2. AnN-pyrimidin-4-yl-N'-sulfonylurea according to claim 1 whereinR₁ ishalogen, nitro, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy,C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxycarbonyl or dimethylsulfamoyl, R₂is halogen, C₁ -C₂ -alkyl, C₁ -C₂ -alkoxy, C₁ -C₂ -haloalkoxy,methylamino or dimethylamino, and R₃ is C₁ -C₂ -alkoxy, trifluoroethoxyor difluoromethoxy. 3.N-(2-Methoxycarbonylphenylsulfonyl)-N'-(2,6-dimethoxy-5-methylpyrimidin-4-yl)-ureaaccording to claim
 1. 4.N-(2-Difluoromethoxyphenylsulfonyl)-N'-(2,6-dimethoxy-5-methylpyrimidin-4-yl)-ureaaccording to claim
 1. 5. A herbicidal and plant-growth regulating orinhibiting composition which contains, as active ingredient, anN-pyrimidin-4-yl-N'-sulfonylurea according to claim 1, together with aninert carrier and/or other additives.
 6. A method of controllingundesirable plant growth, which method comprises applying to the plantsor to the locus thereof a growth-regulating effective amount of anN-pyrimidin-4-yl-N'-sulfonylurea of claim 1, or of a compositioncontaining it as active ingredient.
 7. A method of reducing plantgrowth, which method comprises applying to the plants or to the locusthereof a growth-regulating effective amount of anN-pyrimidin-4-yl-N'-sulfonylurea of claim 1, or of a compositioncontaining it as active ingredient.
 8. A method for the selective, pre-or post-emergence controlling of weeds in crops of cultivated plants,which method comprises applying thereto or to the locus thereof aherbicidally effective amount of an N-pyrimidin-4-yl-N'-sulfonylurea ofclaim 1, of of a composition containing it as active ingredient.